The gold dress this was pure nonsense. We’re answering questions of the ages here at the Straight Dope.
Yes, i think it’s fascinating that some people think it must have been set in the distant past. I don’t get it, but there must be something that gives that impression.
Coming up next: “Billy, Don’t Be a Hero.” Just why did the girl throw the letter away?
That ought to be good for at least a hundred posts, if not more.
That’s what I was thinking as well. It’s sort of an “olde timey” description. Who actually talks like that?
Western Port that “serves 100 ships a day” might imply San Diego, LA, San Francisco, or Seattle, but the tone evokes a smaller, more intimate locale. In my mind something more akin to a New England town lake Gloucester, MA or someplace in Alaska where the seaport is the primary industry and Brandy has few romantic options outside of the sailors who frequent the bar.
The story is contemporary enough that it’s about a single woman tending bar and it doesn’t seem odd. To the extent that half a century ago or longer (1970s) is “contemporary”. But it feels older. No modern references like phones or TV. The song doesn’t describe Brandy walking past yards of intermodal shipping containers.
I think age of steam, not sail. Like I imagine the sailor wearing an old peacoat or something.
It’s also amusing how strenuously some are defending their mental image, almost offended by “the other side.” And I’m following closely to see who makes the best arguments, so I am definitely not above the fray!
Go Old-timey side! We’re number one! We’re number one! 
Grief has driven Brandy into a fantasy world existence because she can’t accept what has happened to the love of her life. The sailors aren’t merchant seamen, they’re military. Brandy’s man was killed in action during the war, but tells everyone that it’s really his love for the sea that prevents him from coming back to her. A few years later, Brandy leaps from the rocky cliffs on the Western Cape to join her lover in eternity.
Why’d they leave the cake out in the rain?
I lean towards the nearly contemporary or at least early 20th century interpretation, not Age of Sail.
But as to this bit:
I don’t think we know anything about the bar except that Brandy is one of the workers there. There might be 2 other bartenders / waitstaff, a male cook, and a male manager on duty. Or the bar may have no food and she is the one and only worker 12 hours a day 7 days a week for an absentee owner. Hell, maybe she owns the place after her father died and willed it to her. Or she started it on her own.
We simply don’t know since the song doesn’t say.
I don’t think that meant “no other workers” . I think it means that Brandy was an unmarried woman tending bar rather than a married woman tending the bar that she and her husband own or a single woman working as a maid or in a factory. I wouldn’t expect a single woman to be tending bar in 1870.
Plausible scenarios, certainly. We don’t know why Brandy works there, just that she works there.
It was an early morning bar room, and the place just opened up.
And the little man come in so fast and started at his cup.
And the broad who served the whisky, she was a big old friendly girl.
And she tried to fight her empty nights by smilin’ at the world.
And she said "Hey Bub, It’s been awhile, since you been around.
Where the hell you been hidin’?
And why you look so down?"
(“Better Place to Be,” by Harry Chapin.)
Good point. I probably misunderstood @msmith537. The lyrics do say
The sailors say, “Brandy, you’re a fine girl” (You’re a fine girl)
What a good wife you would be (Such a fine girl)
Which speaks directly to her marital status. Any woman trying to fend off itinerant sailors would be more inclined to falsely claim to be married than falsely claim to be single. So good bet she really is single.
I guess I don’t find the idea of an unmarried woman tending bar all that outré even back in 1870. Women been working in one role or another in saloons since saloons been invented. To be sure in that era it would mark her out as a “bad” woman, fallen or worse. But a girl’s gotta eat somehow and tending bar is probably better than sewing for a living.
Yeah I didn’t really ever closely listen or analyze the song. I actually heard “my life my love and my lady is the sea” line and pretty much stopped there with any images following from the old sailing ship era that evoked in my head. Now if the line there was “my old lady” a different image would have come up, likely. That I picture a modern sailor saying. 
I don’t argue that it is objectively correct. But that line is what, ehem, anchored my visual context.
Another clue, to me, that it’s from a different era is that he’s simply called a sailor. Would people from the 70’s and onward be referred to that way? While those in the navy obviously are sailors, how often are they called “sailor”?
In my mind, the sailor is quite a bit older than Brandy, has a scruffy beard, and wears dark clothes. He’s been around the block enough times that he realizes that no woman will hold his fascination like the sea does. I’d have a hard time picturing Petty Officer Johnson being so devoted to the ocean going life.
I always pictured it as a east coast/New England port, but that would only be a “western bay” if you were singing the song from a European perspective. The western bay of San Francisco seems too rough. She’s not a Barbary Coast woman. And Looking Glass was from the faraway land of… New Jersey.
PS Jimmy Loves Mary Ann from their second album is good, too. Not as good as Brandy, but still. I have it in my iTunes collection.
We talked with a very drunk British dude who repeatedly told me he was a proper sailor, having survived a hurricane at sea. (The bar was a yacht club bar)
Years later at a different bar, I mentioned “proper sailor” to someone and he immediately knew who I was talking about.
LOL!
I always assumed contemporary (early 70s) Pacific Northwest. Not sure why - never really gave it much thought.
But how often would he get to Spain most likely those sailors are heading to Taiwan or Japan from a western port. Then it’d be a nice jade and ivory locket.
He ordered it from the Sears catalogue.
You have never heard the term “barmaid?” To me that conjures up images of pre-Victorian times. Apparently the term dates back to the 17th century.
But what’s that flower she had on? Could it be a faded rose from days gone by?